反应详情

温度

95 °C

Cuprous iodide (12 mg) and anhydrous potassium carbonate (0.33 g, 2.4 mmol) were placed in a tube (15×2 cm) equipped with a magnetic stirring bar, and 6-ethylmercapto-8-mercapto octanoic acid (Compound (H)) (0.19 g, 0.8 mmol) in 2-methyl-2-butanol (2 mL) was added. The tube was closed with a septum cap and flushed with argon. Ethylene glycol (100 mg, 90 μL, 0.8 mmol) was added via a syringe followed by iodobenzene (164 mg, 90 μL, 0.8 mmol,). The tube was flushed again with argon, then sealed with parafilm and stirred at 95° C. for 38 h. The mixture was cooled to room temperature, and water (15 mL) was added. The pH of the suspension was adjusted to 2 with 2.0 M hydrochloric acid. The mixture was extracted with chloroform (3×10 mL). The combined extracts were dried over magnesium sulfate and filtered, and the solvent was evaporated to yield a yellow oil weighing 0.25 g, TLC (CHCl3—CH3OH—HOAc 100:10:1) and showing a major spot with Rf=0.45, a minor spot with Rf=0.39 and several minor spots. The erode product in chloroform (0.5 mL) was applied to a column (12×2.2 cm) with silica gel 60 (20 g) packed in CHCl3—CH3OH—HOAc (100:5:1). The column was eluted with CHCl3—CH3OH—HOAc (100:10:1). Fractions of 4-5 ml, were collected at a flow rate of 0.5 mL/min. The product was collected in fractions 7-10; colorless oil weighing 140 mg. TLC Rf=0.45 (silica gel: CHCl3—CH3OH—HOAc, 100:10:1); 1H-NMR (CDCl3): δ 7.1-7.4 (m, 5H), 3.08 (td, 2H), 2.6-2.8 (m, 1H), 2.48 (q, 2H), 2.35 (t, 2H), 1.3-1.9 (m, 8H), 1.22 (t, 3H); MS (ESI (−)); 311 (M-1).

1. custom(15×2 cm) equipped with a magnetic stirring bar
2. customThe tube was closed with a septum
3. customcap
4. customflushed with argon
5. customThe tube was flushed again with argon
6. customsealed with parafilm
7. temperatureThe mixture was cooled to room temperature
8. additionwater (15 mL) was added
9. extractionThe mixture was extracted with chloroform (3×10 mL)
10. dry with materialThe combined extracts were dried over magnesium sulfate
11. filtrationfiltered
12. customthe solvent was evaporated
13. customto yield a yellow oil
14. washThe column was eluted with CHCl3—CH3OH—HOAc (100:10:1)
15. customFractions of 4-5 ml, were collected at a flow rate of 0.5 mL/min
16. customThe product was collected in fractions 7-10